House vacation rentals in Southold
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Top-rated house rentals in Southold
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold house rentals
House rentals with a pool
Home in East Hampton
4.93 out of 5 average rating, 107 reviewsPrivate & Pristine with Pool and Kid’s Playard
Home in Water Mill
4.92 out of 5 average rating, 120 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Home in Sag Harbor
4.81 out of 5 average rating, 133 reviewsThanksgiving! Sag Harbor Gem!
Home in Manorville
4.98 out of 5 average rating, 243 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Mastic Beach
4.93 out of 5 average rating, 118 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
Home in Southampton
4.95 out of 5 average rating, 151 reviewsWaterview, DogsStayFree! Kayaks, Ping-Pong
Home in East Hampton
4.98 out of 5 average rating, 128 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in Water Mill
4.92 out of 5 average rating, 119 reviewsAstounding Watermill 5 Bedroom home with Pool
Weekly house rentals
Home in North Fork
5 out of 5 average rating, 10 reviewsSunset Ranch
Home in North Fork
4.98 out of 5 average rating, 53 reviewsVictorian Pearl
Home in North Fork
4.93 out of 5 average rating, 15 reviewsCharming Home in Village Center!
Home in North Fork
5 out of 5 average rating, 11 reviewsModern Farmhouse Oasis in GP Village
Home in North Fork
5 out of 5 average rating, 4 reviewsPeaceful in Peconic
Home in North Fork
4.92 out of 5 average rating, 24 reviewsNorth Fork Farmhouse with Saltwater Pool
Home in North Fork
5 out of 5 average rating, 6 reviewsNorth Fork Farm House
Home in North Fork
4.92 out of 5 average rating, 12 reviewsNorth Fork Sound Front Home with Pool
Private house rentals
Home in North Fork
5 out of 5 average rating, 23 reviewsElegant Victorian in the Heart of Greenport
Home in North Fork
5 out of 5 average rating, 17 reviewsNewly renovated farmhouse - steps to Village
Home in North Fork
5 out of 5 average rating, 12 reviewsPeaceful Guesthouse
Home in North Fork
5 out of 5 average rating, 16 reviewsWaterfront with private dock & bocce court
Home in North Fork
5 out of 5 average rating, 3 reviewsBahia Mar: Beach House, North Fork
Home in North Fork
4.94 out of 5 average rating, 70 reviewsBeach house @ NoFo
Home in North Fork
5 out of 5 average rating, 25 reviewsThe Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Home in North Fork
4.95 out of 5 average rating, 63 reviewsNassau Point, North Fork Home w/ Pool
Quick stats about house rentals in Southold
Total rentals
170 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
50 properties have a pool
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- Rentals with a hot tub Southold
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